Fuel property evaluation of unique fatty acid methyl esters containing β-hydroxy esters from engineered microorganisms

McCormick, Robert L.; Fioroni, Gina M.; Mohamed, Samah Y.; Naser, Nimal; Alleman, Teresa L.; Kim, Seonah; Wang, Ziyu; Lin, Ying; Ju, Yiguang; Kar, Kenneth

doi:10.1016/j.jfueco.2024.100120

Fuel property evaluation of unique fatty acid methyl esters containing β-hydroxy esters from engineered microorganisms

Journal Article · Fri May 10 00:00:00 EDT 2024 · Fuel Communications

DOI:https://doi.org/10.1016/j.jfueco.2024.100120· OSTI ID:2428932

^[1]; ^[1]; ^[1]; ^[1]; Alleman, Teresa L. ^[1]; Kim, Seonah ^[2]; ^[3]; Lin, Ying ^[3]; Ju, Yiguang ^[3]; Kar, Kenneth ^[4]

National Renewable Energy Laboratory (NREL), Golden, CO (United States)
National Renewable Energy Laboratory (NREL), Golden, CO (United States); Colorado State Univ., Fort Collins, CO (United States)
Princeton Univ., NJ (United States)
ExxonMobil Research and Engineering Co., Annandale, NJ (United States)

Unique fatty acid methyl esters (FAME) containing ..beta..-hydroxy esters were produced using an engineered microorganism by glucose fermentation. This study investigated the properties of the unique FAME mixture both neat and in blends with conventional diesel, as well as properties of ..beta..-hydroxy esters. The unique FAME blend contained relatively shorter-chain FAME (average fatty acid chain carbon number 14.6) with 58 % monounsaturated fatty acids and 9 % saturated and monounsaturated ..beta..-hydroxy acid chains. The unique FAME had significantly lower distillation T90 (321 °C versus 352 °C) and higher cetane number (56.7 versus 52) compared to soy biodiesel. Cloud points were within method repeatability. Unexpectedly (because of the lack of methylene-interrupted double bonds), the unique FAME had low oxidation stability (1.5 h) as determined by Rancimat induction period. Stability could be improved through addition of commonly used antioxidants. We speculate that monounsaturated ..beta..-hydroxy FAME may be the source of this instability. Blends with conventional diesel up to 50 vol% showed similar kinematic viscosity (within method repeatability) as blends of conventional FAME. The unique FAME had no effect on distillation T90 even at the 80% blend level. A 30 vol% blend into conventional diesel had a Rancimat induction period of only 2 h, very nearly the same as the neat unique FAME sample. The addition of antioxidants produced blends of acceptable stability. Based on an assessment of the properties of individual ..beta..-hydroxy FAME molecules, they have higher boiling point, higher cloud point, lower cetane number, and potentially lower storage stability than analogous FAME not having the ..beta..-hydroxy group. Removing them from the fuel product in the production process may result in a biodiesel product with superior properties to what is on the market today.

View Accepted Manuscript (DOE)

Research Organization:: National Renewable Energy Laboratory (NREL), Golden, CO (United States)

Sponsoring Organization:: USDOE; Exxon-Mobil Technology and Engineering Company

Grant/Contract Number:: AC36-08GO28308

OSTI ID:: 2428932

Report Number(s):: NREL/JA--4A00-86938; MainId:87713; UUID:552886e9-1fe1-4421-ac24-d24c89b71074; MainAdminId:73185

Journal Information:: Fuel Communications, Journal Name: Fuel Communications Vol. 19; ISSN 2666-0520

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (39)

Thermogravimetric analysis for boiling points and vapour pressure Goodrum, J. W.; Siesel, E. M. Journal of Thermal Analysis, Vol. 46, Issue 5 https://doi.org/10.1007/BF01979239	journal	May 1996
Lipid oxidation: Mechanisms, products and biological significance Frankel, E. N. Journal of the American Oil Chemists' Society, Vol. 61, Issue 12 https://doi.org/10.1007/BF02540830	journal	December 1984
Extraction of Lipids from Municipal Wastewater Plant Microorganisms for Production of Biodiesel Dufreche, Stephen; Hernandez, R.; French, T. Journal of the American Oil Chemists' Society, Vol. 84, Issue 2 https://doi.org/10.1007/s11746-006-1022-4	journal	January 2007
The Effect of Natural and Synthetic Antioxidants on the Oxidative Stability of Biodiesel Tang, Haiying; Wang, Anfeng; Salley, Steven O. Journal of the American Oil Chemists' Society, Vol. 85, Issue 4 https://doi.org/10.1007/s11746-008-1208-z	journal	February 2008
A Comprehensive Evaluation of the Melting Points of Fatty Acids and Esters Determined by Differential Scanning Calorimetry Knothe, Gerhard; Dunn, Robert O. Journal of the American Oil Chemists' Society, Vol. 86, Issue 9 https://doi.org/10.1007/s11746-009-1423-2	journal	June 2009
Biodiesel production from waste cooking oil: 1. Process design and technological assessment Zhang, Y. Bioresource Technology, Vol. 89, Issue 1 https://doi.org/10.1016/S0960-8524(03)00040-3	journal	August 2003
Decarbonising ships, planes and trucks: An analysis of suitable low-carbon fuels for the maritime, aviation and haulage sectors Gray, Nathan; McDonagh, Shane; O'Shea, Richard Advances in Applied Energy, Vol. 1 https://doi.org/10.1016/j.adapen.2021.100008	journal	February 2021
Properties of a new gasoline oxygenate blend component: 3-Hydroxybutyrate methyl ester produced from bacterial poly-3-hydroxybutyrate Wang, Shen Yu; Wang, Zhen; Liu, Ming Ming Biomass and Bioenergy, Vol. 34, Issue 8 https://doi.org/10.1016/j.biombioe.2010.03.020	journal	August 2010
Biodiesel production by in situ transesterification of municipal primary and secondary sludges Mondala, Andro; Liang, Kaiwen; Toghiani, Hossein Bioresource Technology, Vol. 100, Issue 3 https://doi.org/10.1016/j.biortech.2008.08.020	journal	February 2009
Evaluation of alkyl esters from Camelina sativa oil as biodiesel and as blend components in ultra low-sulfur diesel fuel☆ Moser, Bryan R.; Vaughn, Steven F. Bioresource Technology, Vol. 101, Issue 2 https://doi.org/10.1016/j.biortech.2009.08.054	journal	January 2010
Renewable fuels from algae: An answer to debatable land based fuels Singh, Anoop; Nigam, Poonam Singh; Murphy, Jerry D. Bioresource Technology, Vol. 102, Issue 1 https://doi.org/10.1016/j.biortech.2010.06.032	journal	January 2011
The potential of sustainable algal biofuel production using wastewater resources Pittman, Jon K.; Dean, Andrew P.; Osundeko, Olumayowa Bioresource Technology, Vol. 102, Issue 1 https://doi.org/10.1016/j.biortech.2010.06.035	journal	January 2011
A comprehensive chemical kinetic combustion model for the four butanol isomers Sarathy, S. Mani; Vranckx, Stijn; Yasunaga, Kenji Combustion and Flame, Vol. 159, Issue 6 https://doi.org/10.1016/j.combustflame.2011.12.017	journal	June 2012
Effect of the β-hydroxy group on ester reactivity: Combustion kinetics of methyl hexanoate and methyl 3-hydroxyhexanoate Mohamed, Samah Y.; Naser, Nimal; Fioroni, Gina Combustion and Flame, Vol. 258 https://doi.org/10.1016/j.combustflame.2023.113071	journal	December 2023
Storage stability and ageing effect of biodiesel blends treated with different antioxidants Karavalakis, Georgios; Hilari, Despina; Givalou, Lida Energy, Vol. 36, Issue 1 https://doi.org/10.1016/j.energy.2010.10.029	journal	January 2011
Vapor pressure and normal boiling point predictions for pure methyl esters and biodiesel fuels Yuan, W.; Hansen, A.; Zhang, Q. Fuel, Vol. 84, Issue 7-8 https://doi.org/10.1016/j.fuel.2005.01.007	journal	May 2005
Oxidation stability of blends of Jatropha biodiesel with diesel Jain, Siddharth; Sharma, M. P. Fuel, Vol. 90, Issue 10 https://doi.org/10.1016/j.fuel.2011.05.003	journal	October 2011
Chemical compositions, properties, and standards for different generation biodiesels: A review Singh, Digambar; Sharma, Dilip; Soni, S. L. Fuel, Vol. 253 https://doi.org/10.1016/j.fuel.2019.04.174	journal	October 2019
Evaluation of formulation strategies to eliminate the biodiesel NOx effect Szybist, James P.; Boehman, André L.; Taylor, Joshua D. Fuel Processing Technology, Vol. 86, Issue 10 https://doi.org/10.1016/j.fuproc.2004.11.006	journal	June 2005
Saturated monoglyceride effects on low-temperature performance of biodiesel blends Chupka, G. M.; Fouts, L.; Lennon, J. A. Fuel Processing Technology, Vol. 118 https://doi.org/10.1016/j.fuproc.2013.10.002	journal	February 2014
Long-term storage stability of biodiesel and biodiesel blends Christensen, Earl; McCormick, Robert L. Fuel Processing Technology, Vol. 128 https://doi.org/10.1016/j.fuproc.2014.07.045	journal	December 2014
Biodiesel and renewable diesel: A comparison Knothe, Gerhard Progress in Energy and Combustion Science, Vol. 36, Issue 3 https://doi.org/10.1016/j.pecs.2009.11.004	journal	June 2010
Review of biodiesel composition, properties, and specifications Hoekman, S. Kent; Broch, Amber; Robbins, Curtis Renewable and Sustainable Energy Reviews, Vol. 16, Issue 1 https://doi.org/10.1016/j.rser.2011.07.143	journal	January 2012
Overproduction of free fatty acids in E. coli: Implications for biodiesel production Lu, Xuefeng; Vora, Harmit; Khosla, Chaitan Metabolic Engineering, Vol. 10, Issue 6, p. 333-339 https://doi.org/10.1016/j.ymben.2008.08.006	journal	November 2008
Water Contamination Impacts on Biodiesel Antioxidants and Storage Stability Christensen, Earl D.; McCormick, Robert L. Energy & Fuels, Vol. 37, Issue 7 https://doi.org/10.1021/acs.energyfuels.2c03911	journal	March 2023
Life Cycle Greenhouse Gas Emissions of Biodiesel and Renewable Diesel Production in the United States Xu, Hui; Ou, Longwen; Li, Yuan Environmental Science & Technology, Vol. 56, Issue 12 https://doi.org/10.1021/acs.est.2c00289	journal	May 2022
Application of ( R )-3-Hydroxyalkanoate Methyl Esters Derived from Microbial Polyhydroxyalkanoates as Novel Biofuels Zhang, Xiaojun; Luo, Rongcong; Wang, Zhen Biomacromolecules, Vol. 10, Issue 4 https://doi.org/10.1021/bm801424e	journal	April 2009
Lubricity of Components of Biodiesel and Petrodiesel. The Origin of Biodiesel Lubricity Knothe, Gerhard; Steidley, Kevin R. Energy & Fuels, Vol. 19, Issue 3 https://doi.org/10.1021/ef049684c	journal	April 2005
Impact of Antioxidant Additives on the Oxidation Stability of Diesel/Biodiesel Blends Karavalakis, Georgios; Stournas, Stamos Energy & Fuels, Vol. 24, Issue 6 https://doi.org/10.1021/ef1004623	journal	June 2010
Estimation of Density of Biodiesel Phankosol, Suriya; Sudaprasert, Kaokanya; Lilitchan, Supathra Energy & Fuels, Vol. 28, Issue 7 https://doi.org/10.1021/ef501031z	journal	June 2014
Storage Stability of Biodiesel and Biodiesel Blends McCormick, Robert L.; Westbrook, Steven R. Energy & Fuels, Vol. 24, Issue 1 https://doi.org/10.1021/ef900878u	journal	January 2010
Impact of Biodiesel Source Material and Chemical Structure on Emissions of Criteria Pollutants from a Heavy-Duty Engine McCormick, Robert L.; Graboski, Michael S.; Alleman, Teresa L. Environmental Science & Technology, Vol. 35, Issue 9 https://doi.org/10.1021/es001636t	journal	May 2001
Sooting Tendencies of Oxygenated Hydrocarbons in Laboratory-Scale Flames McEnally, Charles S.; Pfefferle, Lisa D. Environmental Science & Technology, Vol. 45, Issue 6 https://doi.org/10.1021/es103733q	journal	March 2011
Microbial production of fatty-acid-derived fuels and chemicals from plant biomass Steen, Eric J.; Kang, Yisheng; Bokinsky, Gregory Nature, Vol. 463, Issue 7280, p. 559-562 https://doi.org/10.1038/nature08721	journal	January 2010
Stability of biodiesel, its improvement and the effect of antioxidant treated blends on engine performance and emission Rashed, M. M.; Kalam, M. A.; Masjuki, H. H. RSC Advances, Vol. 5, Issue 46 https://doi.org/10.1039/C4RA14977G	journal	January 2015
Net-zero emissions energy systems Davis, Steven J.; Lewis, Nathan S.; Shaner, Matthew Science, Vol. 360, Issue 6396 https://doi.org/10.1126/science.aas9793	journal	June 2018
Engineering Escherichia coli for Biodiesel Production Utilizing a Bacterial Fatty Acid Methyltransferase Nawabi, Parwez; Bauer, Stefan; Kyrpides, Nikos Applied and Environmental Microbiology, Vol. 77, Issue 22 https://doi.org/10.1128/AEM.05046-11	journal	September 2011
Thioesterase II of Escherichia coli Plays an Important Role in 3-Hydroxydecanoic Acid Production Zheng, Zhong; Gong, Qiang; Liu, Tao Applied and Environmental Microbiology, Vol. 70, Issue 7 https://doi.org/10.1128/AEM.70.7.3807-3813.2004	journal	July 2004
An Experimental Investigation of the Origin of Increased NO _x Emissions When Fueling a Heavy-Duty Compression-Ignition Engine with Soy Biodiesel Mueller, Charles J.; Boehman, André L.; Martin, Glen C. SAE International Journal of Fuels and Lubricants, Vol. 2, Issue 1 https://doi.org/10.4271/2009-01-1792	journal	June 2009

Similar Records

Fatty acid derived alkyl ether fuels for compression ignition

Patent · Mon Dec 06 23:00:00 EST 2021 · OSTI ID:1860135

Effect of molecular weights of fatty acid esters on cetane numbers as diesel fuels

Journal Article · Sat Jun 01 00:00:00 EDT 1985 · J. Am. Oil Chem. Soc.; (United States) · OSTI ID:6457864

Related Subjects

09 BIOMASS FUELS
carbon neutral fuel
esters
fuel properties
low-carbon liquid fuel
oxidation stability

Fuel property evaluation of unique fatty acid methyl esters containing β-hydroxy esters from engineered microorganisms

Citation Formats

References (39)

Similar Records

Related Subjects